Sodium borohydride → (2-methylquinolin-6-yl)methanol

To a stirred solution of 2-methylquinoline-6-carbaldehyde (1.00 g, 5.8 mmol) in THF (60 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.221 g, 5.8 mmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 1 N aq. HCl solution (10 mL). After stirring for 15 min at RT, the mixture was basified to pH=9 with a 2 N aq. NaOH solution. THF was then removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (200 mL), washed with brine (20 mL), dried over Na2SO4, filtered and concentrated under vacuum to give (2-methylquinolin-6-yl)methanol SLA 47080A as a yellow oil (1.056 g, quant.).

1. temperaturethen cooled in an ice bath
2. custombefore quenching by addition of a 1 N aq. HCl solution (10 mL)
3. stirringAfter stirring for 15 min at RT
4. customTHF was then removed at 40° C. under vacuum
5. extractionthe solution was extracted with CH2Cl2 (200 mL)
6. washwashed with brine (20 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under vacuum

ORD record

ord-749a0a61be634611adbb132d86c4acae

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772316B2